


Firsts - Dean

by reggie



Series: Firsts 'verse [1]
Category: Supernatural
Genre: F/M, First Kiss, First Time, Loss of Virginity, Underage Sex
Language: English
Status: Completed
Published: 2013-08-20
Updated: 2013-08-20
Packaged: 2017-12-24 03:02:58
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 3,239
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/934525
Author URL: https://archiveofourown.org/users/reggie/pseuds/reggie
Summary: <blockquote class="userstuff">
              <p>This is part one of Firsts 'verse chronicling the Winchester boys' first sexual encounters. This chapter deals with Dean's first times. The second will be Sam's and the third will be Wincest but each fic is stand-alone.</p>
<p>Dean pulled her down onto his bed and was almost dizzy from a combination of lust, fear and awe. Although he’d done a lot more than other boys his age, this was the first girl he’d had in his bed...in any bed.</p>
            </blockquote>





	Firsts - Dean

**Author's Note:**

> This is my first time writing porn and it's a little nerve wracking, I hope it's not disappointing. This first story is purely het, the second will be het with a dash of M/M and the third will be pure slash. If you don't like Wincest you only need avoid the third story.

 

 

[](http://s1345.photobucket.com/user/fanficstuff1/media/Banners/firstspt1dean_zps573f495d.jpg.html)

 

Dean had known he was attractive before he had even hit puberty because people constantly said so. From the time he stopped thinking girls were gross, he realized that he could have them eating out of the palm of his hand with his smile and swagger and he used it to full advantage. He was always confident – with the way they lived and the things he’s seen and done, he’d always seemed older than his age. Whatever school he landed in, he’d smile and wink and the girls just ate it up. Even at thirteen he had that whole rebel without a cause thing going so he really had no problem fitting in wherever he went. The girls wanted him and the guys wanted to be like him. He didn’t have much free time though because he had to look after Sammy. Not that he minded – he adored his little brother and Sammy worshiped the ground he walked on.  
  
His first proper kiss was with Sally Kingston when they were living in a trailer park in Oregon. He was not long gone thirteen and she was fifteen and she taught him the fine art of French kissing in the laundry room and let him get to second base that same day. During week two she jerked him off and taught him how to bring her off with his fingers.  It was awesome! On his fourteenth birthday he convinced Rachel McCarthy to give him his first blow job behind the science block at school. By that age he could pretty much get any girl he wanted and he was even getting hit on by guys. He learned quickly that he could flirt with just about anyone to get anything he wanted.  
  
Two weeks after Dean’s fifteenth birthday Sam had asked if he could spend the night at his new friend’s house. Dean knew his father wouldn’t approve but he wasn’t going to be back for a few more days. Sam always found moving around and not having permanent friends really hard so he couldn’t bring himself to say no to those pleading eyes but made him promise to keep it their secret. If dad found out he’d have Dean’s balls.  
  
With nobody to make dinner for he thought he’d take the opportunity to see if Luke was home. Luke was always bragging that his parents would stay out ‘til all hours on a Friday night and he and his older brother would get drunk. Dad was on a hunt and Sammy wasn’t going to be home until lunch time tomorrow so hell yeah, that sounded like fun. As luck would have it Luke wasn’t home. Dean found himself sitting on a bench at the park trying to figure if he could stretch their meager funds enough to go see a movie when he saw her. She was sitting under a tree flicking through a magazine. She had long brown hair tucked behind her ear and she was wearing a skin tight, low cut t-shirt that barely contained her ample breasts. He couldn’t stop staring – man she was hot. She looked up and caught him watching her and even though she was obviously a lot older than him he was cocky enough to flash her his best smile. When she grinned back he sauntered over, “Hey.”  
  
“Hey yourself” She bent forward to retrieve a pack of cigarettes from her bag and he spied a tattoo of a butterfly peeking out from her jeans on her lower back.  
  
“Cool tatt”  
  
“Thanks, ya wanna smoke?”  
  
“Yeah, thanks.”  
  
“I’m Jasmine”  
  
“Dean. Pretty name for a pretty girl”  
  
“Well aren’t you a smooth one,” she let out a husky laugh that had his dick twitching and he flashed another smile. “You’re cute, how old are you?”  
  
He knew he looked older than he was, partly from his recent growth spurt, partly from all of his physical training and partly from his self confidence so he thought he’d see if he could get away with it. Plus, by the way she was staring at his lips he knew she liked what she saw, there was no way he was gonna blow this by telling the truth, “Seventeen.”  
  
“Hmmm, seventeen huh? Really?” She gave him a thorough once over looking a little doubtful but if she didn’t believe him, she didn’t say so.  
  
“How old are you?”  
  
She smiled at that and licked her lips. “Nineteen.”  
  
She commented on his Led Zeppelin T-shirt which led to talking about music and he found they both had very similar musical taste. Dean flirted shamelessly and he was a little surprised when Jasmine flirted right back. He never had a problem getting with girls his own age or even a little older but his mind was blown that a hot nineteen year old babe really seemed into him. After an hour or so of talking and smoking and with his heart hammering in his chest, he leaned forward and softly pressed his lips to hers and she kissed him back. He broke the kiss and put his hand to her cheek and looked at her to gauge her reaction. She flicked her half lidded gaze from his eyes to his mouth and back to his eyes again so he kissed her again lightly touching her bottom lip with his tongue. When she let out a small sigh he deepened the kiss. When they came up for air she suggested that maybe they should take this somewhere else. When he told her he had the apartment to himself and she told him to lead the way he couldn’t believe his luck.  
  
As they entered the apartment she said “So, you said your dad is working out of town. He’s not due back tonight is he?” She sat on the sofa.  
  
He took a couple of his dad’s beers from the fridge and handed her one, “Nah, he’ll be gone for a few more days and my little brother is at a sleep over.” He’d ask Luke’s brother to buy replacement beer for him tomorrow before dad got back. He took a pull from the bottle and sat close beside her.  
  
“So...”  
  
“So...”  
  
He leaned in, cupped the back of her head in his hand and sucked her bottom lip into his mouth. When he snaked his tongue into her mouth she met it with her own eagerly. Soon the kisses became hotter, deeper and more urgent. She swung her leg over his lap and straddled him without breaking contact. All of his blood seemed to rush straight to his dick and he rocked up against her.  He started kissing her neck from just below her ear down to her collarbone and she let out a breathy little moan. He had one hand in the middle of her back and ran the other from her waist over her ribs to her breast feeling her nipple go hard under his palm. When her breath hitched he lightly tweaked it. She ran her hands up under his t-shirt and then tugged on the hem and pulled it up. He raised his arms and let her remove it. Thanks to all of their training he had great muscle tone for his age and she seemed to appreciate it.  
  
“Let me see you,” he said and she pulled her own t-shirt off exposing her tanned skin and pink lace bra. “Damn, you’re hot!” She smiled and dove in for another devouring kiss.  
  
“Should we take this to the bedroom?” she asked and Dean thought he was going to come in his pants right then and there.  
  
“Um, er, yeah, just give me a sec would you, I share a room with my little brother and I just want to make sure it’s not too much of a mess.”  
  
When he got into the room he quickly moved the knife he kept under his pillow and took the knife that was tucked into his boot and put them in the drawer with the gun. He quickly shoved his schoolbooks back into his bag so she wouldn’t see his 9th grade textbooks and did a quick scan of the room. All good.  
  
He returned, took her hand and led her down the short hall. He pulled her down onto his bed and was almost dizzy from a combination of lust, fear and awe. Although he’d done a lot more than other boys his age, this was the first girl he’d had in his bed...in any bed. All of his teenage groping thus far had been rushed and mostly clothed in places like laundry rooms and under the bleachers or behind buildings. He leaned over her, kissed her deeply and slid his hand into the cup of her bra, gently kneading her breast and then pulling the lace back he licked at her nipple. She ran her hand down his flank, over his developing abs and slowly unzipped his fly. When she slid her hand into his boxers he let out a moan. With the stimulation and the thought of where this all might be leading, he had to start cataloging car parts in his head to stop himself from coming. He undid the button of her jeans and when she didn’t protest he pulled down her zip and slipped his hand into her panties. When he felt her wetness he moaned again and when he began rubbing small circles on her clit she let out a small whimper.  
  
She took her hand out from his boxers and pushed him back a little and he thought he had pushed too far until she started to wriggle out of her jeans. Now fantasy was becoming reality as he was pretty sure that he actually was about to get laid. “Jesus,” he breathed and was intensely glad that his dad had given him condoms even though he was slightly embarrassed at the time. He peeled off his own jeans and for all of his bravado he was suddenly struck by nerves. He knew the mechanics of sex, hell he’d had his cock sucked plenty of times but knowing and doing were very different and he really didn’t want to embarrass himself.  
  
Although the only light in the room was coming from the streetlight outside, as Dean was removing his jeans Jasmine could see he was shaking a little and she could see both lust and fear fighting for dominance in his expression. She pulled him down beside her and kissed him. “Oh shit, you’ve never done this before have you?”  
  
Damn, he really, really did not want her to freak out because he was some sort of dorky virgin and leave. “Pfft, of course I have.”  
  
“It’s okay if you haven’t...it’s actually kinda hot.”  
  
For just a moment his swagger broke and she could see the vulnerability on his face. “Well, I’ve done all this and other stuff but no, not all that.” He quickly recovered his too cool for school look. “So, it’s hot huh?”  
  
“Yeah, it really is. So I guess I’m driving then,” she grinned. She pushed him flat on his back and straddled him.  She leaned down and started questioning and kissing “So, how far have you gone?” _Kiss_. She ran her hand over his rock hard cock. “Hand job?” _Kiss_. He nodded. _Kiss_. “Have you been sucked?” _Kiss_. He groaned loudly and once again nodded. Damn it at this rate he was going to come before the main event so he pulled her hand away. That husky laugh was back. “You worried you’re gonna come?” _Kiss_.  He blushed but before he could answer Jasmine asked, “How about I suck you? If you come now you’ll last longer when we fuck.”  
  
“Jesus. Fuck. Yeah,” he answered with an involuntary buck of the hips. “Please, suck me.”  
  
Jasmine sat back up, unhooked her bra and brought Dean’s hands up to remove it. She hovered above his crotch and even through both sets of underwear he could feel her heat. She guided his hands to cup her breasts and encouraged him to gently squeeze her nipples and panted when he did. She leaned forward and put her nipple in his mouth and he swirled his tongue around the hard bud. “OK Dean, Drivers’ Ed time, that feels great. Now suck it and then really gently use your teeth. Oh. Oh yeah. Just like that. Now the other one. Hot damn, your mouth should be illegal.” He smiled and flicked his tongue out.  
  
She ground down once hard on his cock and her wetness soaked through his boxers making his breath hitch. She laid her body flush with his and started to slide his boxers off. He opened his legs so she could settle between them. “Mmmm, you’re big.” Then she engulfed his cock with her hot, wet mouth. She only sucked a few times until Dean stuttered, “I’m gonna...” She took him as far as she could and he shot hot and fast and he couldn’t believe she let him come in her mouth! He was breathing so hard he thought he might hyperventilate and then she was suddenly kissing him and he could taste his own jizz. He couldn’t believe how hot that was.  
  
“Have you ever gone down on a girl, Dean?” Even though he had only just come, his cock twitched. He shook his head and said cockily, “No but I think I’m about to.”  
  
He rolled her onto her back and plunged his tongue into her mouth. She guided his head to her breast again and he laved over her nipple, sucking and nibbling like she showed him before. She writhed beneath him and his head was spinning. He was thinking that this was the best night of his whole life! She nudged his head down and he slipped her panties off and settled between her thighs. He looked up at her and her eyes were dark and glittering and he had no clue as to what he should do. He looked at the small dark thatch of curly hair and the shiny wetness and said, “Teach me” and tentatively lapped at the moisture. The lightly musky scent and the salty taste of her making his heart beat impossibly fast and his dick twitch and begin to fill again.  
  
“Mmmm, that’s good” she cooed. He gently and almost reverently parted her lips so he could see her pussy and licked a stripe over the whole surface making Jasmine moan. “Yeah, that’s nice, do what you feel like and then use your tongue like you did with your fingers. Give me your hand.” He looked up at her and stretched his arm out. She took his hand and put his palm to her mouth and made tight little circles and flicking movements over his palm with her tongue and said, “Do that to my clit”. His cock went from half hard to granite hard and he'd never thought it was possible to be this turned on. He licked around her inner lips and pushed his tongue inside her like he was fucking her with it and she gripped his hair and was making sweet little moans so he figured he was doing alright. Then he licked up to where he thinks her clit is and started to move his tongue like she showed him. She moved his head slightly and then gasped and then he knew he’d gotten exactly the right spot.  
  
He flicked his tongue and she asked him to put a finger inside her and when he did he sucked a bit at the same time and she bucked up hard. He had the winning combination now so he just kept it going and pushed a second finger in. She started to pant heavily so he sped up his fingers and flicked his tongue quickly and suddenly she clenched around his fingers, he looked up at her face and she was making a perfect little ‘O’ with her mouth and when she shuddered she gushed her juices all over his chin. She pushed him away a little so he wiped his mouth and chin and crawled up to kiss her. He was achingly hard so when she said, “Have you got a condom?” he almost fell over his own feet to get to his wallet.  
  
He opened the foil pack and remembering everything from health class he rolled it on and looked at Jasmine. She was still breathless from her orgasm and she looked so goddamn hot he hoped he wasn’t going to shoot his load in the first ten seconds. He was past nervousness now and so horny and ready he just wanted to jump her but he leaned forward and kissed her and she smiled and helped guide him inside. It was tight and so warm and he groaned loudly as he pushed in. He started to move slowly, trying not to come and she wrapped her legs around his thighs and he found his rhythm. He was glad she blew him earlier or he would’ve shot his load the moment he entered her. She was moaning and bucking up to meet his thrusts and all of a sudden her body started to stiffen up and she’s dug her nails into his ass cheeks. She held her breath, then shouted “Oh God” and she shuddered again. He could feel her pulsing around his cock as he thrust wildly and then he was coming so hard he thought he might die.  
  
He slumped forward and almost crushed her. She pushed at him and he realized he was squashing her so he rolled off as he grabbed the condom and pulled out. They were both lying there breathing heavy and she whooped, “Wow, you’re a natural Dean. Are you sure you haven’t done that before?” He felt immense pride at the compliment and gave her a big shit-eating grin, “So do you think I’ll get my license to drive now?” They both started to laugh and she rolled onto her side and put her head on his chest, “I think you’re officially off your learner’s permit now”.  
  
When Sam got home the next day he passed Jasmine on her way down the hall. Dean was standing in the doorway in just a pair of jeans.  
  
“What was Jasmine doing here?”  
  
Dean’s eyebrows shot up. “You know her?”  
  
“Yeah, she’s Ryan’s and Melissa’s sitter. You’re not planning on getting her to look after me?” he scowled, “Dad will kill you if you leave me with a babysitter, Dean.”  
  
“Sammy, she wasn't here about you. Jasmine and I were just having a little fun together.”  
  
“What kind of fun?”  
  
Dean smirked and raised one eyebrow.  
  
“Sure, Dean – as if.” He rolled his eyes. “ You're fifteen and she’s in college. You’re so full of it.”  
  
“Whatever you say, Sammy.”  
  
Dean headed into the bathroom for a shower and Sam went into their bedroom to dump his bag and he spied a pair of little pink lacy panties at the end of his messed up bed. _Holy cow!_  
  
He only knew the basics about sex but it sounded awful and messy and he couldn’t believe Dean had actually done it. Then he screwed up his nose and shouted, “Eeeuw, you’re so gross, Dean! Why did you have to do it in my bed?”  
  
He heard Dean laughing from the bathroom, “Sucks to be you, Sammy!”  
  
 _Fin_


End file.
